4-Fluoroaniline → Picolinafen

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Analogously to Example 4, 6.84 g (25 mmol) of 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyridine, 3.33 g (30 mmol) of 4-fluoroaniline, 2.92 g (27.5 mmol) of sodium carbonate, 5.6 mg (25 μmol) of palladium(II) acetate and 260 mg (0.75 mmol) of tris(4-methoxyphenyl)phosphine in 25 ml of methylcyclohexane were reacted under a CO pressure of 7.5 bar for 20 hours. After cooling to 80° C., the reaction mixture was diluted with 65 ml of warm methylcyclohexane. The salts were filtered off and washed with 10 ml of warm methylcyclohexane. On cooling to 5° C. the product crystallized. The yield was 8.1 g (86 percent) of a light beige solid. The melting point was 104.5° to 105.1° C.

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